Cyprodinil

225.28900

225.29

601-785-8

42P6T6OFWZ

DTXSID1032359

Fine beige powder|White crystalline solid|Powder with agglomerates at 20 °C

2942000000

37.81000

3.47900

Off-white Solid

1.21 g/cm³ @ Temp: 20 °C

75.9 °C

406ºC at 760 mmHg

199.3ºC

1.659

5.77e-05 M|In water, 13 mg/L (pH 7.0); 20 mg/L (pH 5.0) at 25 °C|In ethanol 160, acetone 610, toluene 440, n-hexane 26, n-octanol 140 (all in g/L at 25 °C)|0.013 mg/mL at 25 °C

0-6ºC

8.42E-07mmHg at 25°C

Weak odor

Henry's Law constant = 8.39X10-8 atm-cu m/mole at 25 °C (est)

pKa = 4.44

152.07 Ų [M+H]+ [CCS Type: TW]|177.42 Ų [M+HCOO]-

VAP: 5.1X10-4 Pa (crystal modif. A); 4.7X10-4 Pa (crystal modif B) at 25 °C|log Kow = 3.9 (pH 5.0); 4.0 (pH 7.0); 4.0 (pH 9.0)|Hydroxyl radical reaction rate constant = 2.0X10-10 cu cm/molecule-sec at 25 °C (est)

III

UN 3077

R36/38; R43

S26-S36

Xi

Stable at normal temperatures and pressures.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.|Do not reuse product containers. Dispose of product containers, waste containers, and residues according to local, state, and federal health and environmental regulations.

Incompatible materials: Strong oxidizing agents

USEPA/Office of Pesticide Programs; Joint FAO/WHO Meeting on Pesticide Residues - Pesticide residues in food, Cyprodinil (121552-61-2) (2003)[Available from, as of June 28, 2016: http://www.inchem.org/documents/jmpr/jmpmono/v2003pr03.htm]|USEPA; Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Cyprodinil, Reason for Issuance: Registration (April 6, 1998).[Available from, as of June 24, 2016: https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-288202_06-Apr-98.pdf]

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|H315 (13.97%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 272 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Danger|H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]|P260, P264, P270, P273, P314, P391, and P501

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Coveralls. Shoes plus socks. Waterproof gloves.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.|Control spill at its source and contain to prevent it from spreading, contaminating soil, or entering sewage and drainage systems or any body of water. Clean up immediately. Solid: Sweep up material and place into compatible disposal container. Liquid: Cover entire spill with absorbing material and place into compatible disposal container. Scrub area with hard water detergent. Pick up wash liquid with additional absorbent and place into container. Seal container and arrange for deposition.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for CYPRODINIL (6 total), please visit the HSDB record page.

SEDIMENT: Cyprodinil was not detected in 96 sediment samples collected from 18 sites in the Yarra catchment area of Australia; samples were collected from Sept 2008 to Mar 2009(1). SOIL: Cyprodinil residues were reported at a maximum of about 400 ug/kg in soil sampled from fields along the River Alongos, Spain(2).

IDENTIFICATION AND USE: Cyprodinil is a fine beige powder. It is used as a foliar fungicide in cereals, grapes, pome fruits, stone fruits, strawberries, and vegetables and as a seed dressing on barley; it controls a wide range of pathogens, including Pseudocercosporella herpotrichoides, Erysiphe spp., Pyrenophora teres, Rhynchosporium secalis, and Septoria nodorum. HUMAN EXPOSURE AND TOXICITY: Cyprodinil acts as an aryl hydrocarbon receptor activator, a potential endocrine disrupter, and an extracellular signal-regulated kinase disrupter. Weak androgen receptor binding was shown for cyprodinil. Cyprodinil was genotoxic for HepG2 cells at concentrations 20 uM. ANIMAL STUDIES: In a 28 day gavage study in rats, the LOEL is 100 mg/kg bw/day for rats, based on increased liver weights and abnormalities in liver morphology. In a two-generation reproduction study in rats, the LOEL for maternal systemic toxicity is 4000 (about 326 mg/kg/day) based on lower body weights in the F0 females during the pre-mating period. The NOEL for maternal systemic toxicity is 1000 ppm (about 81 mg/kg/day). The LOEL for reproductive/developmental toxicity is 4000 ppm (about 326 mg/kg/day) based on decreased pup weights (F1 and F2). The NOEL for reproductive toxicity is 1000 ppm (about 81 mg/kg/day). In an 18-month carcinogenicity study in mice, the LOEL is 2000 ppm (males- 212.4 mg/kg/day) based on a dose-related increase in the incidence of focal and multifocal hyperplasia of the exocrine pancreas in males. The NOEL is 150 ppm (males- 16.1 mg/kg/day). This study was tested to adequate levels based on signs of toxicity in males at 2000 ppm and females at 5000 ppm. There was no indication of carcinogenic potential at any dose level. ECOTOXICITY STUDIES: In plants, cyprodinil promoted a copious increase in exudate secretion and caused the most severe collapse of stigmatic cells of all the fungicides evaluated.

... A previous study identified the seven most common pesticide mixtures to which the French population was exposed through food consumption in 2006. The aim of this study was to investigate if the seven mixtures are potentially cytotoxic and genotoxic and if so, whether compounds in a same mixture have a combined effect. The cytotoxicity and genotoxicity of the seven mixtures were investigated with a new assay (gamma-H2AX) using four human cell lines (ACHN, SH-SY5Y, LS-174T, and HepG2). Mixtures were tested at equimolar concentrations and also at concentrations reflecting their actual proportion in the diet. Irrespective of the cell line tested, parallel cytotoxicity of the seven mixtures was observed. Only one mixture was genotoxic for the HepG2 cells at concentrations = 3 uM in equimolar proportion and at 30 uM in actual proportion. Caspase 3/7 activity, the comet assay, and reactive oxygen species production were also investigated using the same mixture and HepG2 cells. Our results suggest that pesticide metabolites from the mixture generated by HepG2 cells were responsible for the observed damage to DNA. Among the five compounds in the genotoxic mixture, only fludioxonil and cyprodinil were genotoxic for HepG2 cells alone at concentrations = 4 and 20 uM, respectively. Our data suggest a combined genotoxic effect of the mixture at low concentrations with a significantly higher effect of the mixture of pesticides than would be expected from the response to the individual compounds.

LD50 Rat oral >2000 mg/kg|LD50 Rat percutaneous >2000 mg/kg|LC50 Rat inhalation >1200 mg/cu m/4 hr

/PLANTS/ Fungicides can be detrimental to flower development, pollen function and fruit set in a number of crops. Almond is a self-incompatible nut crop that has a fruit set of only approx. 30% of the total number of flowers. Thus, interference of pollination and fertilization by fungicide sprays is of concern, and identification of chemicals having the least detrimental effects would be desirable. The objective of this study was to evaluate the effect of fungicide sprays on stigma morphology in almond using a laboratory spray apparatus that simulated field applications. Four fungicides (azoxystrobin, myclobutanil, iprodione and cyprodinil) were applied, and fresh, unfixed stigmatic surfaces were observed using a scanning electron microscope at 4 and 24 hr after spraying. .... Cyprodinil promoted a copious increase in exudate secretion and caused the most severe collapse of stigmatic cells of all the fungicides evaluated. Damage was somewhat localized at 4 hr but more global at 24 hr. ...|/PLANTS/ The beneficial fungus Neozygites floridana kills the two-spotted spider mite Tetranychus urticae, which is a serious polyphagous plant pest worldwide. ... The aim of this study was to conduct a laboratory experiment to evaluate the effect of pesticides used in strawberry and soybean crops on N. floridana. Among the pesticides used in strawberry, the fungicides sulfur and cyprodinil + fludioxonil completely inhibited both the sporulation and conidia germination of N. floridana. ...

Cyprodinil's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 1679-3980(2-3), indicate that cyprodinil is expected to have low to slight mobility in soil(SRC). Volatilization of cyprodinil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 3.68X10-6 mm Hg(4), and water solubility, 13 mg/L(4). Cyprodinil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Mineralization of cyprodinil was reported as 6.3-24.7% in four soils, 54.1-63% was found bound to the same soils(5). These results indicate that the major route of dissipation for cyprodinil is adsorption(5). Cyprodinil had a half-life of 12.5 and 6.5 days in soil under open field and greenhouse conditions, respectively(6). The half-life of cyprodinil was 5.8-15.6 days on soil at two experimental stations in China(7).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 1679-3980(2-3), indicate that cyprodinil is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 3.68X10-6 mm Hg(5), and water solubility, 13 mg/L(5). Cyprodinil is stable to hydrolysis under environmental conditions (pH 5 to 9)(5). According to a classification scheme(6), a BCF of 511 in bluegill sunfish(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The half-life for photodegradation of cyprodinil in water was reported as 13.5 days(5). Biodegradation data in water were not available(SRC, 2016).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyprodinil, which has a vapor pressure of 3.68X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyprodinil is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase cyprodinil may be removed from the air by wet and dry deposition(SRC). Cyprodinil does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of cyprodinil with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyprodinil is stable to hydrolysis under environmental conditions (pH 5 to 9)(2). Cyprodinil does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The BCF of cyprodinil was reported as 511, measured in bluegill sunfish (Lepomis macrochirus)(1). According to a classification scheme(2), this BCF suggests bioconcentration in aquatic organisms is high(SRC).

Koc values of 1679 to 2613 have been reported in eight soils from four vineyards in Spain(1). The Koc of cyprodinil was also reported as 3980(2). According to a classification scheme(3), this Koc range suggests that cyprodinil has low to slight mobility in soil.|Radio-labeled cyprodinil was added to four soils to determine environmental fate processes, soil binding was reported as follows(1):[Table#6645]

The Henry's Law constant for cyprodinil is estimated as 8.4X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 3.68X10-6 mm Hg(1), and water solubility, 13 mg/L(1). This Henry's Law constant indicates that cyprodinil is expected to be essentially nonvolatile from water and moist soil surfaces(2). Cyprodinil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUND WATER: A maximum concentration of 2000 ng/L of cyprodinil was reported in a review of 47 studies published from 1997 to 2013 analyzing Italian ground water samples(1).|SURFACE WATER: Cyprodinil was not detected in surface water samples from Italy as reported in 47 studies published from 1997 to 2013(1). Cyprodinil was not detected (detection limit 0.002-0.004 ug/L) in 96 surface water samples collected from 18 sites in the Yarra catchment area of Australia; samples were collected from Sept 2008 to Mar 2009(2).

Of 173 agricultural products analyzed in 2006 from Japan, four were reported to contain cyprodinil at 1.9-22.2 ng/g(1). Cyprodinil was not detected (detection limit 0.02 mg/kg) in 16 apricot, 19 peach, 7 plum, 23 sour cherry or 27 sweet cherry samples collected from 2012 to 2014 from production farms in Poland(2). Cyprodinil was detected in 7 of 50 ready-to-eat Italian meals (main course, side dish, fruit, bread, wine); samples were collected on Feb 8, May 26, Oct 24 and Dec 21, 2005(3). Cyprodinil was detected in 24 of 47 wine grape (Vitis vinifera L.) samples collected from the 2006 harvest in Slovenia at a concentration range of 0.03-0.40 mg/kg(4).|Cyprodinil was detected in 5.6% of 250 fruit berries grown, collected and analyzed from 2009 to 2011 in south-eastern Poland(1).[Table#6644]|The half-life range of cyprodinil was 9.6-20.8 days on grapes at two experimental stations in China(1). Fourteen days after three low dosage applications the residual concentration was <1.0 mg/kg on grapes(1). The half-lives of cyprodinil on strawberries in China under open field and greenhouse conditions were 14.5 and 5.5 days, respectively(2). The half-lives of cyprodinil on emerald and jewel blueberries were 2.2 and 3.4 days, respectively; samples were collected in Concordia, Argentina(3).|Azoxystrobin, boscalid, cyprodinil, fenhexamid, and pyrimethanil are new generation fungicides extensively employed in order to combat diseases affecting vineyards worldwide. Owing to their physico-chemical characteristics, residues of these compounds on grapes are transferred to must and wine. In this study, a survey of the occurrence of these fungicides in international wines was carried out by using rapid antibody-based assays. Results are discussed as a function of wine type and sample geographical origin. 44.4% of the samples contained at least one of the targets (>10 ug/L). Fungicide residue occurrences were 22.4%, 19.2%, 18.8%, 6.8%, and 1.2% for pyrimethanil, boscalid, fenhexamid, cyprodinil, and azoxystrobin, respectively, while residue contents higher than 100 ug/L were found in 8.4% of the samples. This study shows that contamination of commercial wines with pesticides is an issue of worldwide relevance with potential implications for consumer health and international trade.|Greenhouse studies were conducted to evaluate the dissipation rate kinetics and estimate the behavior of selected pesticides after washing, peeling, simmering, and canning of tomato expressed as processing factor (PF). Two varieties (Marissa and Harzfeuer) were treated by six fungicides: azoxystrobin, boscalid, chlorothalonil, cyprodinil, fludioxonil, and pyraclostrobin at single and double dose and risk assessment defined as hazard quotient was performed. The QuEChERS method was used for sample preparation followed by liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS). The dissipation of fungicides approximately fitted to a first-order kinetic model, with half-life values ranging from 2.49 and 2.67 days (cyprodinil) to 5.00 and 5.32 days (chlorothalonil) for Marissa and Harzfeuer variety, respectively. Results from processing studies showed that treatments have significant effects on the removal of the studied fungicides for both varieties. The PFs were generally less than 1 (between 0.01 and 0.90) and did not depend on variety. The dietary exposure assessed based on initial deposits of application at single and double dose on tomatoes and concentration after each process with PF correction showed no concern to consumer health. Our results would be a useful tool for monitoring of fungicides in tomatoes and provide more understanding of residue behavior and risk posed by these fungicides.

Occupational exposure to cyprodinil may occur through inhalation of dust and vapor, and dermal contact with this compound at workplaces where cyprodinil is produced or used. Monitoring and use data indicate that the general population may be exposed to cyprodinil via ingestion of food containing residual fungicide. (SRC)|Concerns about pesticide drift from neighbouring vineyards affecting children attending school on a farm adjacent to an urban suburb of Cape Town, Western Cape in South Africa were investigated. The study involved a before-after design, measuring levels of environmental exposure before and during pesticide application activities on the neighbouring farms. Samples were collected in air, dust and grass cuttings at the preschool and primary school located on the farms during September-December in 2010 and tested for pesticides using multi-pesticide methods. Eleven different pesticides were detected in the various samples. Six of these chemicals (endosulfan, dimethomorph, penconazole, cyprodinil, boscalid and bromopropylate) were on the spraying schedules of the two farms neighbouring the schools and the timing and location of detection were generally consistent with farm application. Three pesticides detected (chlorpyrifos, cypermethrin, permethrin) are agents commonly used in household applications and one (pyriproxifen) is used in pet treatment agents. Kresoxim-methyl, the other pesticide detected, is likely to come from drift from other farms in the area. The concentration of pesticides was all lower than 0.1 ug/cu m in air and 0.1 ug/kg in dust and grass apart from permethrin and cypermethrin. The findings confirm the presence of drift onto the school premises and concentrations found in this study were generally low in comparison to that detected in other studies. Regular monitoring to track the effectiveness of containment and mitigation measures that reduce drift is recommended.

Cyprodinil was detected at a maximum of 1161 pg/mg in hair samples collected March to Nov 2009 from 18 farm workers(1).

... In rats, radiolabelled cyprodinil administered by gavage as a single dose of 0.5 or 100 mg/kg bw, or as repeated doses of 0.5 mg/kg bw per day for 14 days, was rapidly absorbed from the gastrointestinal tract and excreted. Approximately 75% (range, 71-85%) of an orally administered dose was absorbed over 48 hr. At a dose of 0.5 and 100 mg/kg bw, two plasma level maxima of radioactivity were observed at approximately 0.5-1 hr and 8-12 hr, probably caused by reabsorption of material excreted in the bile. Approximately 92-97% of the administered dose was eliminated within 48 hr in the urine (48-68%), feces (29-47%), and bile (accounting for up to 35.4% of the dose in cannulated rats), with elimination being almost complete by day 7. Seven days after single or repeated oral administration at the lower dose, total tissue residues accounted for 0.15-0.60% of the administered dose. ... Excretion, distribution and metabolite profiles were essentially independent of dose, pretreatment and site of radiolabel, although there were some quantitative sex-dependent differences in urinary metabolites.|After oral administration, CGA 219417 is rapidly absorbed and also rapidly and almost completely eliminated with urine and feces. ... Residues in tissues were generally low and there was no evidence for accumulation or retention of radioactivity.

In studies of metabolism in rats, ... cyprodinil was primarily metabolized by hydroxylation of the phenyl and pyrimidine rings and methyl group, and excreted mainly as glucuronide or sulfate conjugates in urine, feces and bile. Approximately 3-8% of the parent compound was detected in the feces. Excretion, distribution and metabolite profiles were essentially independent of dose, pretreatment and site of radiolabel, although there were some quantitative sex-dependent differences in urinary metabolites.|The metabolic pathways are independent of sex, pre-treatment or dose level administered.|In tomatoes, the metabolism of CGA 219417 proceeded mainly via hydroxylation of the 6-methyl group of the pyrimidine ring as well as hydroxylation of the phenyl & pyrimidine ring.

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/BIOMONITORING/ In the present work, a highly sensitive method based on solid phase microextraction and gas chromatography tandem (triple quadrupole) mass spectrometry was used to test hair samples for 50 pesticides including 39 molecules from different chemical families currently used in agriculture and 11 organochlorines. The population investigated was composed of 18 farm workers who provided hair samples repeatedly collected during the entire treatment period (from March to November 2009). Among the 62 hair samples that were collected, 33 different target molecules were detected. The most frequently detected agricultural pesticides were Diflufenican and Pyrimethanil, two herbicides which were detected in 13 subjects. The concentration in volunteers' hair matched with agricultural activity and the highest concentration was observed for Cyprodinil (1161 pg/mg), an anilinopyrimidine used as a fungicide. ...|/ENDOCRINE MODULATION/ Cyprodinil is a pyrimidinamine fungicide, used worldwide by agriculture. It is used to protect fruit plants and vegetables from a wide range of pathogens. Benzo[a]pyrene (BaP) and 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) are toxic environmental pollutants and are prototypes of aryl hydrocarbon receptor (AHR) ligands. Although the structure of cyprodinil distinctly differs from those of BaP and TCDD, our results show that cyprodinil induced nuclear translocation of the AHR, and induced the transcriptional activity of aryl hydrocarbon response element (AHRE). Cyprodinil induced the expression of cytochrome P450 (CYP) 1A1, a well-known AHR-targeted gene, in ovarian granulosa cells, HO23, and hepatoma cells, Hepa-1c1c7. Its induction did not appear in AHR signal-deficient cells, and was blocked by the AHR antagonist, CH-223191.Cyprodinil decreased AHR expression in HO23 cells, resulting in CYP1A1 expression decreasing after it peaked at 9 hr of treatment in HO23 cells. Dexamethasone is a synthetic agonist of glucocorticoids. Cyprodinil enhanced dexamethasone-induced gene expression, and conversely, its induction of CYP1A1 expression was decreased by dexamethasone in HO23 cells, indicating its induction of crosstalk between the AHR and glucocorticoid receptor and its role as a potential endocrine disrupter. In addition to BaP, TCDD, and an AHR agonist, beta-NF, cyprodinil also phosphorylated extracellular signal-regulated kinase (ERK) in HO23 and Hepa-1c1c7 cells, indicating its deregulation of ERK activity. In summary, our results demonstrate that cyprodinil, similar to BaP, acts as an AHR activator, a potential endocrine disrupter, and an ERK disrupter.|/ENDOCRINE MODULATION/ ... The transactivation potential of the pesticides Acorit, Frupica, Steward, Reldan, Switch, Cantus, Teldor, and Scala and their active compounds (hexythiazox, mepanipyrim, indoxacarb, chlorpyrifos-methyl, cyprodinil, fludioxonil, boscalid, fenhexamid, and pyrimethanil) were tested on human estrogen receptor alpha (ERalpha), androgen receptor (AR) and arylhydrocarbon receptor (AhR) in vitro. Relative binding affinities of the pure pesticide constituents for AR and their effect on human breast cancer and prostate cancer cell lines were evaluated. Residue concentrations of Switch's ingredients were below maximum residue limits. Fludioxonil and fenhexamid were ERalpha agonists (EC50 -values of 3.7 and 9.0 uM, respectively) and had time-dependent effects on endogenous ERalpha-target gene expression (cyclin D1, progesterone receptor, and nuclear respiratory factor 1) in MCF-7 human breast cancer cells. Fludioxonil, mepanipyrim, cyprodinil, pyrimethanil, and chlorpyrifos-methyl were AhR-agonists (EC50s of 0.42, 0.77, 1.4, 4.6, and 5.1 uM, respectively). Weak AR binding was shown for chlorpyrifos-methyl, cyprodinil, fenhexamid, and fludioxonil. Assuming a total uptake which does not take metabolism and clearance rates into account, our in vitro evidence suggests that pesticides could activate pathways affecting hormonal balance, even within permitted limits, thus potentially acting as endocrine disruptors.|/GENOTOXICITY/ ... A previous study identified the seven most common pesticide mixtures to which the French population was exposed through food consumption in 2006. The aim of this study was to investigate if the seven mixtures are potentially cytotoxic and genotoxic and if so, whether compounds in a same mixture have a combined effect. The cytotoxicity and genotoxicity of the seven mixtures were investigated with a new assay (gamma-H2AX) using four human cell lines (ACHN, SH-SY5Y, LS-174T, and HepG2). Mixtures were tested at equimolar concentrations and also at concentrations reflecting their actual proportion in the diet. Irrespective of the cell line tested, parallel cytotoxicity of the seven mixtures was observed. Only one mixture was genotoxic for the HepG2 cells at concentrations = 3 uM in equimolar proportion and at 30 uM in actual proportion. Caspase 3/7 activity, the comet assay, and reactive oxygen species production were also investigated using the same mixture and HepG2 cells. Our results suggest that pesticide metabolites from the mixture generated by HepG2 cells were responsible for the observed damage to DNA. Among the five compounds in the genotoxic mixture, only fludioxonil and cyprodinil were genotoxic for HepG2 cells alone at concentrations = 4 and 20 uM, respectively. Our data suggest a combined genotoxic effect of the mixture at low concentrations with a significantly higher effect of the mixture of pesticides than would be expected from the response to the individual compounds.|/ALTERNATIVE and IN VITRO TESTS/ Fenhexamid and cyprodinil are antifungal agents (pesticides) used for agriculture, and are present at measurable amounts in fruits and vegetables. In the current study, the effects of fenhexamid and cyprodinil on cancer cell proliferation and metastasis were examined. Additionally, the protein expression levels of cyclin D1 and cyclin E as well as cathepsin D were analyzed in BG-1 ovarian cancer cells that express estrogen receptors (ERs). The cells were cultured with 0.1% dimethyl sulfoxide (DMSO; control), 17beta-estradiol (E2; 10-9 M), and fenhexamid or cyprodinil (10-5 - 10-7 M). Results of a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay showed that fenhexamid and cyprodinil increased BG-1 cell proliferation about 1.5 to 2 times similar to E2 (5 times) compared to the control. When the cells were co-treated with ICI 182,780 (10-8 M), an ER antagonist, the proliferation of pesticide-treated BG-1 cells was decreased to the level of the control. A wound healing assay revealed that the pesticides reduced the disrupted area in the BG-1 cell monolayer similar to E2. Protein levels of cyclin D1 and E as well as cathepsin D were increased by fenhexamid and cyprodinil. This effect was reversed by co-treatment with ICI 182,780. In a xenograft mouse model with transplanted BG-1 cells, cyprodinil significantly increased tumor mass formation about 2 times as did E2 (6 times) compared to the vehicle (0.1% DMSO) over an 80-day period. ... Cyprodinil also induced cell proliferation along with the expression of proliferating cell nuclear antigen (PCNA) and cathepsin D in tumor tissues similar to E2. Taken together, these results imply that fenhexamid and cyprodinil may have disruptive effects on ER-expressing cancer by altering the cell cycle- and metastasis-related gene expression via an ER-dependent pathway.

cyprodinil

Cyprodinil Technical (Syngenta Crop Protection, LLC): Active ingredient: Cyprodinil 99.0%.|Vangard WG Fungicide (Syngenta Crop Protection, LLC): Active ingredient: Cyprodinil 75.0%.|Switch 62.5WG (Syngenta Crop Protection, LLC): Active ingredient: Fludioxonil 25.0%; Cyprodinil 37.5%.|Inspire Super (Syngenta Crop Protection, LLC): Active ingredient: Difenoconazole 8.4%;Cyprodinil 99.0%.|For more Formulations/Preparations (Complete) data for CYPRODINIL (8 total), please visit the HSDB record page.

This study reports a method based on CE-MS/MS detection developed for the multiresidue determination of seven pesticides (amidosulfuron,cyprodinil, cyromazine, imazaquin, pirimicarb, demethyl pirimicarb, procymidone) and eight residues of veterinary drugs ... , whose contents are regulated by the EU Council Regulations no. 396/2005 and no. 2377/90, in animal edible tissues. Milk samples were extracted with ACN and the extract was cleaned up using an Oasis hydrophilic-lipophilic balance SPE cartridge. The proposed method was validated in accordance with the European Commission Decision 657/2002. MS/MS experiments, using an IT analyzer, operating in multiple reaction monitoring mode, were carried out to achieve the minimum number of required identification points. Recovery data were also satisfactory, with values higher than 78% for most pesticides and veterinary drugs extracted from milk spiked at half the maximum residue limit established for the studied compounds. The RSD% (n = 5) were lower than 13 and 15% for intra-day and inter-day assays, respectively. The method was applied to establish the occurrence of the studied pesticides in 100 milk samples, attaining the determination of pesticide and veterinary drug residues in milk in the low ug/kg range.|An analytical methodology using automatic thermal desorption (ATD) and GC/MS was developed for the determination of 28 pesticides /including/ ... cyprodinil ... . This methodology was developed to evaluate the indoor and outdoor atmospheric contamination by nonagricultural pesticides. Pesticides were sampled passive sampling tubes containing Tenax adsorbent. Since most of these pesticides are polar ... , a derivatization step is required. For this purpose, a silylation step using N-(t-butyldimethylsilyl)-N-methyltrifluoroacetamide (MtBSTFA) was added before thermal desorption. This agent was chosen since it delivers very specific ions on electronic impact (m/z?=?M-57). This method was established with special consideration for optimal thermal desorption conditions (desorption temperature, desorb flow and duration; trap heating duration and flow; outlet split), linear ranges, limits of quantification and detection which varied from 0.005 to 10 ng and from 0.001 to 2.5 ng, respectively, for an uncertainty varied from 8 to 30%. The method was applied in situ to the analysis of passive tubes exposed during herbicide application to an industrial site in east of France.|A novel microextraction technique combining magnetic solid-phase microextraction (MSPME) with ionic liquid dispersive liquid-liquid microextraction (IL-DLLME) to determine four fungicides is presented in this work for the first time. The main factors affecting the extraction efficiency were optimized by the one-factor-at-a-time approach and the impacts of these factors were studied by an orthogonal design. Without tedious clean-up procedure, analytes were extracted from the sample to the adsorbent and organic solvent and then desorbed in acetonitrile prior to chromatographic analysis. Under the optimum conditions, good linearity and high enrichment factors were obtained for all analytes, with correlation coefficients ranging from 0.9998 to 1.0000 and enrichment factors ranging 135 and 159 folds. The recoveries for proposed approach were between 98% and 115%, the limits of detection were between 0.02 and 0.04 ug/L and the RSDs changed from 2.96 to 4.16. The method was successfully applied in the analysis of four fungicides (azoxystrobin, chlorothalonil, cyprodinil and trifloxystrobin) in environmental water samples. The recoveries for the real water samples ranged between 81% and 109%. The procedure proved to be a time-saving, environmentally friendly, and efficient analytical technique.|An up-and-down-shaker-assisted dispersive liquid-liquid microextraction (UDSA-DLLME) method coupled with gas chromatography-mass spectrometry was developed for the determination of fungicides (cyprodinil, procymidone, fludioxonil, flusilazole, benalaxyl, and tebuconazole) in wine. The developed method requires 11 uL of 1-octanol without the need for dispersive solvents. The total extraction time was approximately 3 min. Under optimum conditions, the linear range of the method was 0.05-100 ug/L for all fungicides and the limit of detection was 0.007-0.025 ug/L. The absolute and relative recoveries were 31-83% and 83-107% for white wine, respectively, and 32-85% and 83-108% for red wine, respectively. The intra-day and inter-day precision were 0.5-7.5% and 0.7-6.1%, respectively. Our developed method had good sensitivity and high extraction efficiency. UDSA-DLLME is a desirable method in terms of performance and speed.|For more Analytic Laboratory Methods (Complete) data for CYPRODINIL (7 total), please visit the HSDB record page.

To measure dermal exposure of a non-agricultural occupationally exposed population to pesticides, a new method has been developed for analysis of 13 pesticides from different classes (fungicides, herbicides, insecticides) on dermal patches. The method includes extraction of the patches and analysis of the pesticides by GC-MS and/or HPLC-fluorescence. Water-soluble pesticides (glyphosate and glufosinate) on patches were ultrasonically extracted twice with ultra-pure water for 10 min and analyzed by HPLC-fluorescence after derivatisation with FMOC. Organic-soluble pesticides (bifenthrin, cyprodinil, difufenicanil, fludioxonil, oxadiazon, pyriproxyfen, clopyralid, 2,4-D, fluroxypyr, 2,4-MCPA, and triclopyr) were extracted ultrasonically twice for 10 min with 70:30 dichloromethane-acetonitrile and analyzed by GC-MS directly or after derivatisation with N-methyl-N-tert-butyldimethylsilyltrifluoroacetamide. Detection limits varied between 3 and 4 ug/L for water-soluble pesticides and between 1 and 10 ug/L for organic-soluble pesticides.

Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Cyprodinil has known environmental transformation products that include 3-(4-cyclopropyl-6-methylpyrimidin-2-ylamino)phenol, 4-cyclopropyl-6-methyl-pyrimidine-2-ylamine, and 6-cyclopropyl-2-phenylamino-pyrimidin-4-yl)-methanol.|Cyprodinil has known environmental transformation products that include CGA 249287, CGA 275535, CGA 304075, CGA 304076, and CGA 321915.